Asymmetric epoxidation using iminium salt organocatalysts featuring dynamically controlled atropoisomerism

Philip C. Bulman Page; Christopher J. Bartlett; Yohan Chan; David Day; Phillip Parker; Benjamin R. Buckley; Geracimos A. Rassias; Alexandra M. Z. Slawin; Steven M. Allin; Jérôme Lacour; André Pinto

doi:10.1021/jo300915u

Asymmetric epoxidation using iminium salt organocatalysts featuring dynamically controlled atropoisomerism

Philip C. Bulman Page, Christopher J. Bartlett, Yohan Chan, David Day, Phillip Parker, Benjamin R. Buckley, Geracimos A. Rassias, Alexandra M. Z. Slawin, Steven M. Allin, Jérôme Lacour, André Pinto

Research output: Contribution to journal › Article › peer-review

49 Citations (Scopus)

Abstract

Introduction of a pseudoaxial substituent at a stereogenic center adjacent to the nitrogen atom in binaphthyl- and biphenyl-derived azepinium salt organocatalysts affords improved enantioselectivities and yields in the epoxidation of unfunctionalized alkenes. In the biphenyl-derived catalysts, the atropoisomerism at the biphenyl axis is controlled by the interaction of this substituent with the chiral substituent at nitrogen.

Original language	English
Pages (from-to)	6128-6138
Number of pages	11
Journal	The Journal of Organic Chemistry
Volume	77
Issue number	14
DOIs	https://doi.org/10.1021/jo300915u
Publication status	Published - 2012

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10.1021/jo300915u

Cite this

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title = "Asymmetric epoxidation using iminium salt organocatalysts featuring dynamically controlled atropoisomerism",

abstract = "Introduction of a pseudoaxial substituent at a stereogenic center adjacent to the nitrogen atom in binaphthyl- and biphenyl-derived azepinium salt organocatalysts affords improved enantioselectivities and yields in the epoxidation of unfunctionalized alkenes. In the biphenyl-derived catalysts, the atropoisomerism at the biphenyl axis is controlled by the interaction of this substituent with the chiral substituent at nitrogen.",

author = "{Bulman Page}, {Philip C.} and Bartlett, {Christopher J.} and Yohan Chan and David Day and Phillip Parker and Buckley, {Benjamin R.} and Rassias, {Geracimos A.} and Slawin, {Alexandra M. Z.} and Allin, {Steven M.} and J{\'e}r{\^o}me Lacour and Andr{\'e} Pinto",

year = "2012",

doi = "10.1021/jo300915u",

language = "English",

volume = "77",

pages = "6128--6138",

journal = "The Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "14",

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TY - JOUR

T1 - Asymmetric epoxidation using iminium salt organocatalysts featuring dynamically controlled atropoisomerism

AU - Bulman Page, Philip C.

AU - Bartlett, Christopher J.

AU - Chan, Yohan

AU - Day, David

AU - Parker, Phillip

AU - Buckley, Benjamin R.

AU - Rassias, Geracimos A.

AU - Slawin, Alexandra M. Z.

AU - Allin, Steven M.

AU - Lacour, Jérôme

AU - Pinto, André

PY - 2012

Y1 - 2012

N2 - Introduction of a pseudoaxial substituent at a stereogenic center adjacent to the nitrogen atom in binaphthyl- and biphenyl-derived azepinium salt organocatalysts affords improved enantioselectivities and yields in the epoxidation of unfunctionalized alkenes. In the biphenyl-derived catalysts, the atropoisomerism at the biphenyl axis is controlled by the interaction of this substituent with the chiral substituent at nitrogen.

AB - Introduction of a pseudoaxial substituent at a stereogenic center adjacent to the nitrogen atom in binaphthyl- and biphenyl-derived azepinium salt organocatalysts affords improved enantioselectivities and yields in the epoxidation of unfunctionalized alkenes. In the biphenyl-derived catalysts, the atropoisomerism at the biphenyl axis is controlled by the interaction of this substituent with the chiral substituent at nitrogen.

U2 - 10.1021/jo300915u

DO - 10.1021/jo300915u

M3 - Article

SN - 0022-3263

VL - 77

SP - 6128

EP - 6138

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 14

ER -